Pyridine → HCID 12948391, compound

HRID 1414842Notes

Reaction equation

HRID 1414842 reaction equation
[C:1]([NH:10][NH2:11])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].[C:12](O)(=[O:24])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23].N1C=CC=CC=1.S(Cl)(Cl)=O>ClC1C=CC=CC=1>[C:1]([NH:10][NH:11][C:12](=[O:24])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4]

Participants

6

Reactant 4

HCID 1049PyridineHCID 3893Lauric AcidHCID 13637Salicylic acid, hydrazideHCID 24386Thionyl Chloride

Product 1

HCID 12948391HCID 12948391, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

15.2 g (0.1 mol) of salicylic acid hydrazide and 20.0 g (0.1 mol) of lauric acid are suspended in 200 ml of chlorobenzene, 2.0 g (0.025 mol) of pyridine are added and the mixture is heated to the boil. 13.1 g (0.11 mol) of thionyl chloride are added dropwise at this temperature. The product separates out initially as a turbidity and then as a flocculent precipitate. After boiling for 1 hour the mixture is cooled and the product is filtered off and washed with a little benzene and then with petroleum ether. N-Salicyloyl-N'-lauroyl-hydrazine of melting point 158° C is thus obtained in a yield of 53%. The product can be recrystallised from ethylene glycol monomethyl ether.

Workup

  1. temperaturethe mixture is heated to the boil
  2. temperaturethe mixture is cooled
  3. filtrationthe product is filtered off
  4. washwashed with a little benzene

Sources & evidence

ORD record
ord-fc6fb0b9dde640f1bf18744b978b8f55
Source dataset
uspto-grants-1977_01
Patent number
US04002680

Reaction notes

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